Diisopropylethylamine → 3-(7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-4-methoxy-cyclobut-3-ene-1,2-dione

HRID 1678234Notes

Reaction equation

HRID 1678234 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:15])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.[CH3:20][O:21][C:22]1[C:23](=O)[C:24](=[O:28])[C:25]=1[O:26]C.C(N(CC)C(C)C)(C)C>CO>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:15][C:23]3[C:24](=[O:28])[C:25](=[O:26])[C:22]=3[O:21][CH3:20])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 59023728HCID 59023728, compound

Product 1

HCID 590239873-(7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-4-methoxy-cyclobut-3-ene-1,2-dioneYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A vial containing a solution of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 0.020 g, 0.075 mmol), 3,4-dimethoxy-3-cyclobutene-1,2-dione (0.011 g, 0.077 mmol), N,N-diisopropylethylamine (14 μL, 0.080 mmol) and MeOH (1.5 mL) was shaken at ambient temperature for about 16 hours then filtered to give 3-(7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-4-methoxy-cyclobut-3-ene-1,2-dione (0.022 g, 78%) as a tan solid; RP-HPLC (Table 1, Method e) Rt 1.80 min, m/z (ESI+) 375.9 (M+H)+.

Workup

  1. filtrationthen filtered

Sources & evidence

ORD record
ord-5bb5291de6eb4d9e94451a07839c42e0
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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